Triethylphosphonoacetat
ETHYL 2-(DIETHOXYPHOSPHORYL)ACETATE · ETHYL DIETHYLPHOSPHONOACETATE · Triethyl phosphonacetate · Ticagrelor Impurity 150 · Triethyl phosphonoacetat · CarbethoxyMethyldiethyl Phosphonate · DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER · DIETHYL ETHOXYCARBONYLMETHYLPHOSPHONATE
Identifikatoren & physikalische Daten
| CAS No. | 867-13-0 |
|---|---|
| Summenformel | C8H17O5P |
| Durchschnittliche Molmasse | 224,19 g/mol |
| Monoisotopische Masse | 224,08136027 g/mol |
| SMILES | CCOC(=O)CP(=O)(OCC)OCC |
| InChIKey | GGUBFICZYGKNTD-UHFFFAOYSA-N |
| PubChem CID | 13345 |
| ChEMBL | CHEMBL3185304 |
| EC No. | 212-757-6 |
| DTXSID | DTXSID4041573 |
| Lokaler Name | Triethylphosphonoacetat |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 61,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 206 |
| Stoffklassen | Other Classes -> Organophosphates, Other |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Clear light yellow liquid[Acros Organics MSDS] |
| Collision Cross Section | 143.7 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID4041573] |
| Schmelzpunkt | -24°C |
| Siedepunkt | 142-145 °C9 mm Hg(lit.) |
| Dichte | 1.13 g/mL at 25 °C(lit.) |
| Dampfdruck | 0.61Pa at 25℃ |
| Brechungsindex | n20/D 1.431(lit.) |
| Flammpunkt | 165°C |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)Slightly miscible with water. |
| Aggregatzustand | Liquid |
| Wichte | 1.130 |
| Farbe | Clear |
| BRN | 1343714 |
| InChI | 1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3 |
| InChIKey | GGUBFICZYGKNTD-UHFFFAOYSA-N |
| SMILES | CCOC(=O)CP(=O)(OCC)OCC |
| LogP (Verteilungskoeffizient) | 1.13 at 30℃ |
| CAS Datenbank | 867-13-0(CAS DataBase Reference) |
| EPA chemische Informationen | Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (22.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 70 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, (diethoxyphosphinyl)-, ethyl esterRegulation (EC) No 1935/2004 (amended)Status: Active Update: 19-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11013Acetic acid, (diethoxyphosphinyl)-, ethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Gefahrenübersicht | Oral lethal-dose (rat) > 500 mg/kg[RTECS] An irritant that may cause serious eye injury[Acros Organics MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (22.9%) |
| Toxicity Data | LCLo (mouse) = 1,180 mg/m3/10min |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3082 9/PG 3 |
| Zollcode | 29310095 |
| RTECS-Nr. | AG9800000 |
| R-Sätze (R) | 51/53-36/37/38 |
| Gefahrensymbole | N,Xi,Xn |
| hazard_note | Harmful |
| Sicherheitshinweise (S) | 61-37/39-26-36 |
| Gefahrenklasse | 9Eye Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Beschreibung
Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification. This compound can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl, the resulting alkene formed is usually the E alkene and is generated with excellent regioselectivity. It can synthesize β-Keto Phosphonates via an acylation reaction of triethyl phosphonoacetate with carboxylic acid chlorides in the presence of magnesium chloride-triethylamine followed by decarbethoxylation. Acylation of triethyl phosphonoacetate using magnesium ethoxide affords acyl phosphonoacetates, which, on treatment with catalytic p-TsOH in water, are converted into 2-aryl-2-oxoalkylphosphonates[1-2].
Verwenden
Triethyl phosphonoacetate serves as a reactant used in Horner-Wadsworth-Emmons reactions, Tsuji-Trost type reactions, Intramolecular Heck-type cyclization and isomerizations and Intramolecular aryne-ene reactions. In Horner-Wadsworth-Emmons reaction, it is utilized as a reagent to prepare chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.